Synthetic fatty alkyl and alkenyl ether glycerophospholipids with potential anti-tumor properties have been reported in the literature. See, for example, F. Paltauf, Chem. Phys. Lipids 74, 101-139 (1994). The compound 1-O-octadecyl-2-O-methyl-sn-glycero-3-phosphocholine (ET 18-OCH.sub.3) has markedly potent anti-tumor activity. See R. Andreesen, "Ether Lipids in the Therapy of Cancer," Prog. Biochem. Pharmacol. 22, 118-131 (Karger, Basel 1988). Treatment of cancer with a fatty alkyl ether glycero-phosphoethanolamine component is also disclosed in U.S. Pat. No. 4,372,949. Halo substituted cytostatic analogs are described by H. Brachwitz et al., Chemistry and Physics of Lipids 31, 33-52 (1982). Glycerophospholipids bearing a C.sub.10-24 alkyl ether substituent in the 1-position, a cyclic amido group in the 2-position, and a cyclic ammonio group as part of the phosphoethanolamino function in the 3-position of the glyceryl backbone are described in U.S. Pat. No. 4,650,791. Also disclosed in Pat. No. 4,650,791 are synthetic intermediates wherein the substituents are as described in the preceding sentence herein except that there is an hydroxyl group at the 3-position or hydroxyl groups at both the 1-position and the 3-position of the glyceryl backbone. Glycerophosphoethanolamines bearing a non-cyclic, substituted amino substituent in the 2-position and a lower C.sub.1-5 alkyl ether substituent in the 1-position of the glyceryl backbone are disclosed in U.S. Pat. No. 5,116,992.
Applicants disclose for the first time herein that the novel fatty alkyl and alkenyl ether glycerophosphoethanolamines of the invention, which bear a 3-(2-imidazolinyl)-2-imidazolinyl or 2-imidazolinyl substituent on the ethanolamine nitrogen, and the pharmaceutically acceptable salts thereof, also possess anti-tumor-activity. Surprisingly, in addition, these novel fatty alkyl and alkenyl ether glycerophosphoethanolamines and salts have been discovered to also possess anti-psoriatic, anti-inflammatory, and anti-asthma activities.
The novel compounds and salts of the invention are also useful for treatment and prophylaxis of viral infections, as disclosed in the commonly owned, co-pending U.S. patent application filed on the same day as this Application, having the Title "Method for Treating Viral Infection" and Attorney Docket No. 43549/204. This commonly owned, co-pending Application is incorporated herein by reference in its entirety.